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Check out the local scene at Schooner Wharf Bar

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Local Entertainers
  • Robert Albury Band
  • Michael McCloud
  • Mike Lee
  • Fritz
Favorite Happy Hours
  • Kelly’s Caribbean Bar, Grill & Brewery (4PM-7PM) $2 microbrews, $2.50 well, $3 margaritas & $4.50 for 1 lb wings
  • Conch Republic Seafood Co. (4PM-7PM) BYGO (Buy One Get One)
  • Dante’s (M-F 4PM-8PM) 40%-50% off drinks (4PM-7PM) Raw Bar $.67 each clams, oysters, shrimp
  • Half Shell Raw Bar (4:30PM-6:30PM) $2 domestic beer, $2.75 well, $1.75 draft & $.50 each oysters

entertainmenticonKEY WEST ENTERTAINMENT

Key West, long known for its plethora of bars and nightclubs is all centered on Duval Street. Stroll down this main drag and you will find anything from comedy to jazz to retro to transvestite shows. What more could anyone ask for?
Now, I am not recommending it, but there are many people that do the Duval Crawl – stop in and hit every bar on Duval from one end to the other. The one that is still standing (which is the key word) when you reach the southernmost tip is the winner. Here are a few of the stops along the way with a few quieter corners to search out.

801 Bourbon Bar & Cabaret
801 Duval Street
A local gay bar but a fun place to visit whether gay or straight. Nightly drag shows are at 9 & 11PM in the upstairs cabaret, performed by veterans who are entertaining and funny.  It really is a great show!
Happy hour daily from 1PM-8PM and karaoke every Thursday & Sunday at 6PM.

Afterdeck Bar/ Louie's Backyard
700 Waddell Avenue
afterdeck bar Located behind the wooden A-frame building that houses the famous Louie’s Backyard restaurant and the Upper Deck Wine Bar is a large wooden deck that overlooks the ocean. Grab a seat and let the worries of the day fade away as you enjoy the warm tropical breezes and the spectacular view while sipping on your favorite cocktail. You will feel a million miles away from the rowdiness of Duval - the perfect ending to another day in paradise.

Captain Tony’s Saloon
428 Greene Street
captaintonys The original Ernest Hemingway hangout (and where he met his 3rd wife back in 1936) and the place where Jimmy Buffett wrote “Last Mango in Paris.” A real locals bar with a comfortable and cozy atmosphere (if you call a gravestone next to the pool table cozy?) where you can relax and listen to the local musicians that play nightly. Sip your drink under the huge hanging tree then take a good look up at the ceiling – decorated with license plates, dollar bills, bras and business cards (who would have thunk it?)  On the way out it is a tradition to try tossing a coin into the mouth of the fish (and remember to stand backwards).

Durty Harry’s /Rick’s
202 Duval Street
durtyharrysSharing a small alley way are two great entertainment spots – Durty Harry’s & Ricks. With 6 different venues & 10 bars combined, Ricks (with 3 bars) has live entertainment downstairs and a DJ & dance floor upstairs . Stand on the balcony upstairs to get some air and see what is happening elsewhere on Duval.  Check out the all you can drink for $10 until 11PM (good deal if you can get it) It is definitely a younger crowd and gets pretty rowdy. If you came to Key West to party you will love this spot!

Grand Vin
1107 Duval Street
grandvinOpen until midnight, this upscale wine bar is the perfect place to relax.  Seating available on the balcony (best seat in the house) or inside. No wine snobs here, just a cozy place to have a few drinks with friends. You will probably meet the owner and his wife who are extremely nice people & great to chat with – almost feels like a rerun of "Cheers"

Green Parrot Bar
601 Whitehead Street
greenparrot A staple of Key West since 1890 and voted one of  Playboys top 20 bars in America . A laid back, tropical  open air bar with pool tables, pinball machines & darts. Lots of local flavor with fair priced drinks and great rock music. There is no food served here but there is free popcorn with your drinks.  Catch the Friday jam sessions at 5:30PM. Note: Cash only

hogsbreath

Hog’s Breath Saloon
400 Front Street
Live entertainment, relaxed atmosphere and friendly bartenders – a great time is always had by all.   Get one of their world renowned  t-shirts with their tag line “Hog’s breath is better than no breath at all.” Hit the happy hour from 5PM-7PM nightly.

 

Irish Kevin’s Bar
211 Duval Street
irishkevins
Always a fun place to visit with talented and funny entertainment nightly. Can get  a little raunchy (more so as the night goes on) but all in the name of fun. Holds many forms of drinking contests (some you have never thought of before) with lots of audience participation.

 

Island Dogs Bar
505 Front Street
islanddogsbarGreat little open air bar with good prices and friendly staff. A good place to start & end your evening (open until 4AM) with some of the best late night food on the island. Sit on the porch or at the bar and listen to the nightly entertainment, not too loud so you can really chill.

 

Krawl Off Duval
506 Southard Street
Get away from the madness on Duval and enter this low key beer mecca just off the main street. Krawl Off Duval was awarded best new bar in Key West 2012, after being open about a year, and is a small friendly place with fantastic deals with a great mix of locals and vacationers. They have an entire wall and a half of beer as well as more behind the bar with an excellent variety of cans and bottles. They also have a nitrogen tap in addition to the regular. You can sit on their nice porch or enjoy a beer upstairs in the lounge (although there is no service upstairs). Relax and enjoy the atmosphere and, if you are not into beer, don't be afraid as they also have a few wines on hand. Enjoy their BOGO Happy Hour from 4:30PM-6:30PM everyday. There is no food served here but they are located right next door to Four Buoys Wings and Weiners and across from Mr. Z's Pizza.

 

La Te Da
1125 Duval Street
Situated towards the south end of Duval sits this landmark establishment. You will enjoy visiting any of the 3 bars or the cabaret. Clientele is a mixed crowd, from  gay to straight.  The cabaret highlights such diverse entertainment as renowned female impersonators, headline comedians and Broadway stars.  Head into the Crystal Room for a pre-show drink and to mix with the stars.  If  a drink is all you want, try the Terrace Bar, a shady area protected by trellises and plantation shutters with its beautiful mahogany and glass backed bar or the Piano Bar, adorned with original Picasso sketches and  Spanish statues.

Lazy Gecko
203 Duval Street
lazygeckoSharing a small alley way are two great entertainment spots – Durty A tropical island bar that makes you feel like one of the locals. Tucked into the midst of the Duval madness you will find this bar a great place to cool down on a hot day or chill in the evening, people watch and listen to the live music. They have a great Happy Hour, BOGO, from 5PM-8PM daily and 5PM-12PM Sunday and Monday. Twelve flavors of frozen daiquiris available in addition to their good strong drinks. You might have to watch it if you are not a Boston Red Sox fan as they claim to be the southernmost fan base. Food, such as pizza, burgers and sandwiches, is also available.

Rick’s/Durty Harry’s
202 Duval Street
ricksSharing a small alley way are two great entertainment spots – Durty Harry’s & Ricks. With 6 different venues & 10 bars combined, Ricks (with 3 bars) has live entertainment downstairs, usually classic and contemporary rock,  and a DJ & dance floor upstairs . Stand on the balcony upstairs to get some air and see what is happening elsewhere on Duval.  Check out the all you can drink for $10 until 11PM (good deal if you can get it) Also save the cup your beer came in and you get refills for $1 off.  It is definitely a younger crowd and gets pretty rowdy. If you came to Key West to party you will love this spot!

Rick’s Tree Bar
202 Duval Street
treebar Located at the entrance to Rick's and Durty Harry's entertainment complex is one of the simplest bars in all the keys - just a bar with 8 stools, smack dab in the middle of Duval (across from Sloppy Joes). The perfect place to chill with one of their signature cocktails - a key lime colada, an excellent margarita or a perfect bloody mary (or go for all three!). At night it is the place to see and be seen. Note: Their restroom is easily accessible to the public.

Rum Barrel (Pat Croce’s)
528 Front Street
rumbarrelGreat fun on the upstairs patio. Enjoy the live nightly music, cool breezes, great view & good drinks.  They also have the largest selection of rum in the world. Ask to see the "Rum Bible" with a list of over 100 of the best rums in the world (and you can taste every one of them)

 

Schooner Wharf Bar
202 William Streetschoonerwharf
Be transported back to the old Key West before it became a tourist haven. Enjoy this rustic, laid back, tiki-style bar situated right on the waterfront in the Historic Seaport district. Live music runs day and night with extended happy hours. (Watch for Michael McCloud, who usually starts at noon, playing popular 60's & 70's music Buffett style)

Sloppy Joe’s
201 Duval Street
sloppyjoes Located on this very spot since 1937! Featuring outstanding entertainment beginning at noon every day and rocking into the night until 2AM with plenty of room for dancing.(Look for the Robert Albury Band - fanastic!) Always crowded &  noisy  with good drinks at a fair price.  Enjoy their main bar or Joe’s tap room which features a variety of crafted beers.

Smokin' Tuna Saloon
4 Charles Street
smokin tuna saloon A great little outdoor/indoor bar with no cover charge (unless a special recording artist is playing), plenty of space and always a good band playing (sets at 2PM,6PM and 9PM). The two bar areas offer plenty of seating and an enormous tree in the middle of the place adds charm. So join the locals here where dress is casual, drinks are reasonable and service is fast and friendly. There is a restaurant and raw bar as well that serves until 10PM, bar is open until 2AM.


rumbar

Speakeasy Inn & Rum Bar
1117 Duval Street
A small and cozy rum bar off the beaten track. Frequented mostly by locals and guests of the inn, quite a friendly group , it is a great  place for a night cap. There are literally hundreds of types of rum to choose from but do try a shot of Bahama Bob’s Root juice. Wohoo!

 

The Bull & Whistle Bar (locally known as The Bull)
224 Duval Street (corner of Duval & Caroline Streets)thebull
 A laid back bar with plenty of local flavor. In fact, it is one of the oldest open air bars in Old Town. The Bull offers a great rotation of live entertainment day & night, coupled with great drink specials & great service.
On the second floor is the Whistle Bar with a balcony that is perfect for people watching along Duval Street. They also have foosball tables, pool tables & darts.
On the 3rd floor is the Garden of Eden, Duval Streets only clothing optional bar.

The Porch (Wine Bar)
429 Caroline street
theporchAh, a refined, quiet bar with a wonderful ambiance and a great selection of wines and micro-brewed beers. Great place to avoid drunks as they could never find the entrance. It is located in a beautiful historic plantation house that sits on the corner of Duval and Caroline. Enter the house and take the first door on your left.  Nestled behind some lush landscaping is a beautiful outdoor porch area and some inside seating as well.  Staff is friendly, prices are good and the cool décor gives off a very welcoming vibe. Open until 1AM, 2AM on Friday and Saturday. No food is served here.

Virgilio’s Cocktail Lounge
524 Duval Street
A cozy backyard martini bar with seating set up under the trees. Located behind  La Trattoria, an excellent Italian restaurant, they offer live jazz and blues music. A new local hot spot for the town!

White Tarpon
700 Front Street #107
whitetarponA small and cozy wine shop and bar combination conveniently located right next to the Harbor Walk. Open 6AM-10PM daily this bar/deli combo serves a great breakfast at reasonable prices to grab and go before your morning excursion. Later in the day it becomes a cozy bar serving great martinis (try their key lime martini) and wine in a friendly, relaxing, uncrowded atmosphere. You can even go into the deli next door and choose cheeses and meats which they will plate for you and deliver to the bar at no extra charge.